Cigar Aficionado

It's early on a Friday afternoon and the Hyatt Lake Las Vegas crawls with card counters. Some of the smartest players in the business have swarmed this off-Strip hotel/casino, and, not surprisingly, many are operating under various pseudonyms. There's the diminutive and bearded Richard Munchkin. Stanford Wong, a famous blackjack strategist and author, is anything but Asian. And Anthony Curtis is not the child of a mother obsessed with Hollywood icons.

Big personalities are on the strut and cleverly conceived disguises abound: one player has a hippie-hair wig, a blacked-out tooth and the put-on demeanor of a pint-sized biker. Another's tipped his brownish locks with gray and inserted strips of baby-bottle nipples into his nostrils to pug out his nose. Under most circumstances, this crowd would represent a financial nightmare for any gambling establishment. Not today, however; these top-flight players are here to compete against one another rather than the house in the Ultimate Blackjack Tour.

The organizers—veteran gambler and Tour founder and president Russ Hamilton, entertainment attorney John Moonves and TV producer Houston Curtis—are offering more than $1.3 million in prize money for this invitational event. They're shooting it with the intention of landing a television deal, anticipating that the show will make blackjack as universally beloved as small-screen poker. Invited to help along this process is a who's who of Texas Hold'em stars: Phil Hellmuth, David "Devilfish" Ulliott and Annie Duke.

In today's seven preliminary tournaments, each player receives $25,000 in chips, betting limits range from $500 to $25,000, and a total of 30 hands will get played (with each table's lowest-stacked players eliminated after hands eight, 16 and 25). The object is to finish with as many chips as possible—which necessitates strategically betting in such a way that you maintain a lead over your opponents while minimizing your risk of ruin. The two players with the most chips at each table move on to a semifinal tourney. Then, the top six finishers from each of the seven days of play (filling a total of 42 seats, plus seven players who will have qualified online) earn a seat in the finals, scheduled to be taped two weeks later in Los Angeles, with a first prize of $300,000.

Several weeks earlier, when Hamilton asked me to compete in the preliminaries at the Hyatt, I jumped at the opportunity. In preparation, I spent a few weeks crash-coursing on how to play optimally (Wong's Casino Tournament Strategy has long been considered the bible) and got blackjack sensei Rick Blaine (author of recently published Blackjack Blueprint) to spend a couple nights running through some rudimentary concepts with me.

In Blaine's living room blackjack pit, I learned that it's best to start off slow but to quickly get aggressive if I'm behind as an elimination round looms. Blaine talked about the Secret Bet, a showy Ultimate Blackjack innovation in which each player has an opportunity to write down one bet and make it without others at the table seeing the amount being wagered (save it for the end, advised Blaine). And he offered strategies for holding on to a lead. "Usually," he said, "there are like results, meaning that if you win, your opponent will win as well. When you get ahead, mirror his bets and there's a good chance that you'll hang on to your lead." To say that the lessons make me seasoned, or even competent, is an exaggeration. Although I now feel as if I have a clue, I also expect to be pretty much winging it and do not anticipate getting very far against what promises to be stiff competition. Lingering in my mind, however, is one particular scenario: I have $30,000, another player has $20,000 and a third has $40,000. If we are going into an elimination round, what is the proper bet? I get all kinds of answers: $11,000 (to prevent the guy in last place from catching up), $10,000 (to push if you both win, and to give me the win in the event of a swing), and bet it all (some people can't help but go for broke). When I run into lanky Stanford Wong at the tournament, I pose the question to him. He answers without hesitation: "Nine thousand dollars is the proper bet."

I tell him that I don't get it. With that amount it seems as though I'd be setting myself up to lose if the person with $20,000 bets it all. "I don't mind answering your question," Wong replies, sounding a little testy. "But I'm not going to argue with you about it. We did computer simulations and came to this conclusion. That is the right bet."

Unconvinced, I pose the question to a guy who calls himself Hollywood Dave. Spiky-haired and displaying a flashy fashion sense that is straight out of the New Wave '80s, he offers a different take. "You make a big bet, like $12,000, press the short-stacked player to make a minimum bet [in the hope that you'll both lose, which would leave you with $18,000 and him with $19,500], and then surrender [removing your bet in exchange for giving up half of it]. It guarantees you the win. It is what's called a surrender trap."

Clearly, I have a lot to learn. And when I find myself sitting at a tournament table flanked by Wong and Anthony Curtis, along with poker star Phil "The Unabomber" Laak in the number one seat, I don't have to ask anyone to identify the underdog at this table. Miraculously, however, through a couple of smart wagers (one of which, Curtis marvels, is "the perfect-sized bet") and selective aggressive play, I wind up finishing second to the Unabomber and move on to the semifinals. If I win or place at the next table, I'll receive $2,000 and will be heading off to L.A. to take a shot at the $300,000. But it won't be easy. Among those I'll be up against are two notorious poker pros, Lane Flack and Alex Brennes, a woman named Ophelia whose boyfriend is a well-known card counter ("She's been well schooled," warns Blaine, shaking his head), and, scariest of all, a top-flight, muscled-up blackjack master by the name of Michael Castellana. Spotting his name on the seating list, Blaine ruefully says, "You're playing for second place." Fine, I think, second place will still get me to L.A., a prospect that begins to look more promising as the number of competitors at my table dwindles. In the 25th round, I double down with 15 (obviously an unconventional play, but perfectly sensible under tournament conditions and necessary to prevent my elimination). I draw a 5, dispatching the fourth-place player who leaves with a trail of artfully spouted F-bombs, all aimed at me, and I now feel as if I have a shot.

I've actually got the most chips at the table with only four hands to go. Castellana makes huge bets and goes on to win the next two hands (failing to follow Blaine's advice, I played more conservatively and now trot behind him in second place). Then, on the 29th hand, leading Brennes by $3,000 (and feeling as if L.A. just might be my destiny), I match his $4,000 bet. He doubles down and wins both hands. I lose and suddenly, going into the final round, I am in last place, trailing the second-place player by $9,000. I definitely got unlucky, but, in retrospect, made a critical error in failing to protect my lead by matching Castellana's big bets.

As the final and decisive hand is about to be dealt, I am not in great shape. But my situation is far from insurmountable. I step back from the table to make my secret bet and have a couple of options. I can place a minimum wager of, say, $1,000, assume that Brennes will bet $17,000 (to cover my $25,000-max bet if we both win), and go for the low. In that case, if we both lose, I'll finish in second place. But if we both win, I'll be out of the tournament. The thought of hitting a blackjack and still losing this thing bugs me for reasons that are totally nonmathematical. So I let my ego get the best of me and make a maximum bet. Brennes makes his secret bet, while Castellana (who's now got a big stack and had used his secret bet earlier) pushes forward a medium-sized wager that insures he'll be covered for either first or second place. The cards come and Castellana gets an 18, Brennes has 14, I have a pair of 2s and the dealer shows a 7.

I am first to act (which is the worst possible position to be in) and completely unsure of what to do. Split the 2s? That is the perfect basic strategy play. But Brennes's 14 doesn't look too good for him. The dealer's 7, I figure, will force him to hit. With only 20 seconds to calculate a strategy, and woefully unprepared for being in such a situation, I opt not to split and take a hit. The thinking here is that if I split and lose either hand, then things are essentially over. But if I can just make a single, potentially winning hand with the two 2s, well, then Brennes will have to get lucky with his 14.

I scratch the felt and the dealer slides me a 9, which would have been a great card had I split. My heart begins to break a little. Then comes a 2, giving me a total of 15. I feel compelled to hit and draw a picture card. Busted. I curse myself for failing to bet the minimum with Brennes showing a 14. But then he makes a very smart play (which would have decimated my chance to win here, even with a miniscule bet): he surrenders, getting back half of his money and clinching second place with a guaranteed $50,500. So now it is officially over for me. I'm out of the tournament. No playing in L.A. No shot at the big money. No $2,000 guaranteed. Instantly I'm depressed. I become even more so when I run into Ophelia and her card-counting boyfriend at the Hyatt bar. She can't believe that I didn't split. She keeps explaining why it would have been the better move and insists that I had been given a golden opportunity to snag second place.

Then her boyfriend, who's absorbed more than his fair share of bad beats, admonishes her, saying, "The guy feels awful enough already. Give him a break." Maybe he's right, but so is she. To have increased my shot at winning, I needed to do two things: get as much money on the table as possible and pile on the uncertainty. Splitting would have done the former, and doubling down with the subsequent 11 would have accomplished both goals (doubled cards are dealt face down). Then Brennes would have been forced to hit or possibly even double down with 14.

Rick Blaine comes over, hears about the botched move and advises me to shrug it off. "Yeah," he says, "you needed to get more money in there. You should have split. You needed to double down with a lot of hands that you wouldn't normally do it with. But you also have to look at how well you did. You made it a lot further than some of the most experienced players [including Blaine himself]. It was your first tournament and you did great."

"You're not pissed at me?" I ask, feeling as if I've let down someone who put time into teaching me.

"Pissed?" he responds, sounding incredulous. "I'm proud of you, man. You did great."

I feel a little better, still angry with myself for not thinking things through more clearly, but adjusting to the reality of being bounced. Hollywood Dave hears the scenario, and he offers a philosophical response. "You've gotta figure that you used up your karma when you doubled down on the 15. You shouldn't have lived after that hand."

I order a Scotch and drink to karma and my next shot at winning big bucks on the Ultimate Blackjack Tour.

A couple weeks after my inglorious flameout, when the tournament moves to a soundstage at CBS Studios in West Hollywood, I am chagrined to be in the wings instead of at a table. Frankly, I was so outplayed at the Hyatt that I really don't deserve the seat. Nevertheless, the experience in Vegas did serve to immerse me in the ways of tournament blackjack, leaving me with a decent understanding of the game and its strategies.

For five days here in L.A., on a high-tech stage set, complete with red velvet curtains and swirling lasers, 49 tournament hotshots have spent afternoons and evenings angling for a chance to win $300,000. On the last day of the finals, winners from each of those seven tournaments crowd around a single championship table and prepare to take a shot at the money. Remaining in action are two Daves (hyperkinetic Hollywood Dave, who sports a tight pullover shirt and black leather wristbands to go with his spiky hair, and David Matthews, a lanky dude who is not the famous singer but a former professional gambler who now works for a gambling-related publisher); Rock 'n' Roll Darrell Arnold, who's got black hair streaked with red and more tattoos than a card counter could catalog; blackjack nerd Ken Smith; pimped-out looking Tyrone Jackson; an elegant Asian woman who goes by the name of Adriana Jade; and Monica Reeves, a tyro blackjacker whose boyfriend is the professional poker player Jim "Krazy Kanuck" Worth (at least one fan in the online world has joked that the statuesque Reeves ought to be nicknamed "Big Pair").

None of the contestants are exactly shy. Right from the start they are all perfectly comfortable in soliciting high fives and cheers from the studio audience. Following a particularly strong play, Hollywood Dave autographs a card and flips it into the cheap seats. On the sixth hand (an elimination round), miniskirted Monica asks the crowd whether she should go all in. They roar affirmatively. And she is happy to have listened as she lucks into an 18 against the dealer's 5. But after the under-card reveals itself to be an ace, and a 3 comes on the hit, well, it's bye-bye Monica.

A couple hands later, Tyrone Jackson busts out after mistakenly going all in (he meant to hold back $1,000 in chips). Following Tyrone's departure, Ken Smith loses most of his stack and Hollywood Dave gleefully taunts, "You must feel sick. Like you want to vomit in your shoes."

By the 16th hand, Hollywood Dave is out of the game and so is Smith. The competition is down to David Matthews, Adriana Jade and Rock 'n' Roll Darrell. All three, to varying degrees, are blackjack experts. They've played tournaments before and are unlikely to get rattled by the money at stake, the bright lights or the crowd. But no matter how steady these three may feel, one of them will be eliminated this round.

Because Rock 'n' Roll Darrell is trailing significantly on hand 16, he pushes his entire stack ($89,000) into the betting circle. In second place, Matthews is nearly a lock to survive this round and risks a minimum bet of $1,000. Adriana, in first place, is a lock and she wagers $16,000. It works for two of the players: When Rock 'n' Roll Darrell stands on 13 and the dealer makes an 18, he struts offstage with a sign of the devil cockily flashed toward the audience.

By hand 26, the final elimination round, a winner will be declared. But in reality, it doesn't even take that long. Adriana loses three hands in a row, busts out on round 20 and leaves David Matthews the only remaining player. He jumps skyward, gives her an enormous bear hug, does a victory lap around the set and, no doubt, spends the rest of the day trying to figure out how he's going to spend his 300 grand.

Michael Kaplan is Cigar Aficionado's gambling columnist.